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Article ; Online: Stable isotope synthesis of glycine transporter 1 inhibitor Iclepertin (BI 425809) and its major metabolites.

Latli, Bachir / Hrapchak, Matt J / Chevliakov, Maxim / Samankumara, Lalith P / Frutos, Rogelio P / Lee, Heewon

Journal of labelled compounds & radiopharmaceuticals

2023 Volume 66, Issue 13, Page(s) 414–427

Abstract: Stable isotope labeled Iclepertin (BI 425809, 1) and its major metabolites are needed as internal standards in bioanalytical studies. BI 425809 consists of two main building blocks, 5-methylsulfonyl-2-[(1R)-2,2,2-trifluoro-1-methyl-ethoxy]benzoic acid (2) ...

Abstract	Stable isotope labeled Iclepertin (BI 425809, 1) and its major metabolites are needed as internal standards in bioanalytical studies. BI 425809 consists of two main building blocks, 5-methylsulfonyl-2-[(1R)-2,2,2-trifluoro-1-methyl-ethoxy]benzoic acid (2) and 3-[(1R,5R)-3-azabicyclo[3.1.0]hexan-5-yl]-5-(trifluoromethyl)isoxazole (3) linked to each other via an amide bond. We used fluoro[
MeSH term(s)	Glycine Plasma Membrane Transport Proteins ; Carbon Isotopes/chemistry ; Amides
Chemical Substances	BI 425809 ; Glycine Plasma Membrane Transport Proteins ; Carbon-13 (FDJ0A8596D) ; Carbon Isotopes ; Amides
Language	English
Publishing date	2023-09-20
Publishing country	England
Document type	Journal Article
ZDB-ID	196095-7
ISSN	1099-1344 ; 0362-4803 ; 0022-2135
ISSN (online)	1099-1344
ISSN	0362-4803 ; 0022-2135
DOI	10.1002/jlcr.4063
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Article ; Online: Synthesis of BI 894416 and BI 1342561, two potent and selective spleen tyrosine kinase inhibitors, labeled with carbon 14 and with deuterium.

Latli, Bachir / Hrapchak, Matt J / Samankumara, Lalith P / Fandrick, Daniel R / Pennino, Scott / Lee, Heewon / Song, Jinhua J

Journal of labelled compounds & radiopharmaceuticals

2023 Volume 66, Issue 4-6, Page(s) 155–168

Abstract: R)-4-((R)-1-((6-(1-[tert-butyl]-1H-pyrazol-4-yl)-2-methyl-2H-pyrazolo[3,4-d]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one (BI 894416, 1) and (R)-4-((R)-1-((6-(1-[tert-butyl]-1H-pyrazol-4-yl)-2,3-dimethyl-2H-indazol-4-yl)oxy)ethyl)pyrrolidin-2-one (BI 1342561, ...

Abstract	(R)-4-((R)-1-((6-(1-[tert-butyl]-1H-pyrazol-4-yl)-2-methyl-2H-pyrazolo[3,4-d]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one (BI 894416, 1) and (R)-4-((R)-1-((6-(1-[tert-butyl]-1H-pyrazol-4-yl)-2,3-dimethyl-2H-indazol-4-yl)oxy)ethyl)pyrrolidin-2-one (BI 1342561, 2) are two new potent and selective spleen tyrosine kinase inhibitors developed to treat severe asthma. Both compounds have similar structures and they differ only in the bicyclic moiety 2-methyl-2H-pyrazolo[4,3-c]pyridine in 1 versus 2,3-dimethyl-2H-indazole in 2. In the carbon 14 synthesis, 1-(1-[tert-butyl]-1H-pyrazol-4-yl)ethan-1-one-1-
MeSH term(s)	Carbon Radioisotopes/chemistry ; Deuterium ; Tyrosine Kinase Inhibitors ; Spleen
Chemical Substances	Carbon Radioisotopes ; Deuterium (AR09D82C7G) ; Tyrosine Kinase Inhibitors
Language	English
Publishing date	2023-04-24
Publishing country	England
Document type	Journal Article
ZDB-ID	196095-7
ISSN	1099-1344 ; 0362-4803 ; 0022-2135
ISSN (online)	1099-1344
ISSN	0362-4803 ; 0022-2135
DOI	10.1002/jlcr.4024
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Article: Synthesis of Sterically Congested Carbamates of Carbohydrates through Organic Base Catalysis

Chen, Anji / Wang, Dan / Samankumara, Lalith P. / Wang, Guijun

Synthesis

2019 Volume 51, Issue 15, Page(s) 2897–2908

Abstract: 4,6- O -Benzylidene acetal protected α-methoxy d -glucose and d -glucosamine are useful building blocks for the syntheses of carbohydrate derivatives and functional molecular assemblies. In this research, we have developed a general method for the ... ...

Abstract	4,6- O -Benzylidene acetal protected α-methoxy d -glucose and d -glucosamine are useful building blocks for the syntheses of carbohydrate derivatives and functional molecular assemblies. In this research, we have developed a general method for the preparation of C-3 carbamate derivatives of densely functionalized glucose and glucosamine with isocyanates using organic bases as catalysts. Without a suitable catalyst, the C-3 hydroxy group of the glucosamine derivative could not be converted into the corresponding carbamates when treated with isocyanates. Several organic bases were screened as the catalysts for the reactions, and we discovered that 5.0 mol% of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was an effective catalyst for the carbamoylation reaction. A library of both alkyl and aryl carbamate derivatives of the two sterically congested carbohydrates have been effectively synthesized using the current method.
Keywords	carbamates ; isocyanates ; glucosamine ; glucose ; organocatalysis
Language	English
Publishing date	2019-04-16
Publisher	© Georg Thieme Verlag
Publishing place	Stuttgart ; New York
Document type	Article
ZDB-ID	2033062-5
ISSN	1437-210X ; 0039-7881
ISSN (online)	1437-210X
ISSN	0039-7881
DOI	10.1055/s-0037-1612425
Database	Thieme publisher's database

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Article: Rational Design of New Dihydrobenzooxophosphole-Based Lewis Base Organocatalysts.

Qu, Bo / Samankumara, Lalith P / Saha, Anjan / Schumer, Mac G / Han, Zhengxu S / Haddad, Nizar / Busacca, Carl A / Yee, Nathan K / Kozlowski, Marisa C / Song, Jinghua J / Senanayake, Chris H

Synlett : accounts and rapid communications in synthetic organic chemistry

2021 Volume 31, Issue 6, Page(s) 587–591

Abstract: A series of new dihydrobenzooxophosphole-based Lewis Base organocatalysts were designed and synthesized. They are demonstrated effective in trichlorosilane-mediated stereoselective conjugate reductions of C=C bonds. DFT calculations reveal that the ... ...

Abstract	A series of new dihydrobenzooxophosphole-based Lewis Base organocatalysts were designed and synthesized. They are demonstrated effective in trichlorosilane-mediated stereoselective conjugate reductions of C=C bonds. DFT calculations reveal that the strong hydrogen bond between the amide linker and the chloride on silicon in the transition state contributes to the high reactivity of the catalyst
Language	English
Publishing date	2021-02-04
Publishing country	Germany
Document type	Journal Article
ZDB-ID	2042012-2
ISSN	1437-2096 ; 0936-5214
ISSN (online)	1437-2096
ISSN	0936-5214
DOI	10.1055/s-0039-1690851
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Article ; Online: Synthesis of Chiral 1,2-Amino Alcohol-Containing Compounds Utilizing Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation of Unprotected α-Ketoamines.

Mangunuru, Hari P R / Terrab, Leila / Janganati, Venumadhav / Kalikinidi, Nageswara Rao / Tenneti, Srinivasarao / Natarajan, Vasudevan / Shada, Arun D R / Naini, Santhosh Reddy / Gajula, Praveen / Lee, Daniel / Samankumara, Lalith P / Mamunooru, Manasa / Jayaraman, Aravindan / Sahani, Rajkumar Lalji / Yin, Jinya / Hewa-Rahinduwage, Chathuranga C / Gangu, Aravind / Chen, Anji / Wang, Zhirui /

Desai, Bimbisar / Yue, Tai Y / Wannere, Chaitanya S / Armstrong, Joseph D / Donsbach, Kai O / Sirasani, Gopal / Gupton, B Frank / Qu, Bo / Senanayake, Chris H

The Journal of organic chemistry

2024 Volume 89, Issue 9, Page(s) 6085–6099

Abstract: Herein, we disclose a facile synthetic strategy to access an important class of drug molecules that contain chiral 1,2-amino alcohol functionality utilizing highly effective ruthenium-catalyzed asymmetric transfer hydrogenation of unprotected α- ... ...

Abstract	Herein, we disclose a facile synthetic strategy to access an important class of drug molecules that contain chiral 1,2-amino alcohol functionality utilizing highly effective ruthenium-catalyzed asymmetric transfer hydrogenation of unprotected α-ketoamines. Recently, the COVID-19 pandemic has caused a crisis of shortage of many important drugs, especially norepinephrine and epinephrine, for the treatment of anaphylaxis and hypotension because of the increased demand. Unfortunately, the existing technologies are not fulfilling the worldwide requirement due to the existing lengthy synthetic protocols that require additional protection and deprotection steps. We identified a facile synthetic protocol via a highly enantioselective one-step process for epinephrine and a two-step process for norepinephrine starting from unprotected α-ketoamines
MeSH term(s)	Hydrogenation ; Catalysis ; Amino Alcohols/chemistry ; Amino Alcohols/chemical synthesis ; Ruthenium/chemistry ; Stereoisomerism ; Molecular Structure ; Amines/chemistry
Chemical Substances	Amino Alcohols ; Ruthenium (7UI0TKC3U5) ; Amines
Language	English
Publishing date	2024-04-22
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.4c00045
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Article: Optimization of 1,2,4-Triazole-Based p97 Inhibitors for the Treatment of Cancer.

ACS medicinal chemistry letters

2023 Volume 14, Issue 7, Page(s) 977–985

Abstract: The AAA+ ATPase p97 (valosin-containing protein, VCP) is a master regulator of protein homeostasis and therefore represents a novel target for cancer therapy. Starting from a known allosteric inhibitor, NMS-873, we systematically optimized this scaffold, ...

Abstract	The AAA+ ATPase p97 (valosin-containing protein, VCP) is a master regulator of protein homeostasis and therefore represents a novel target for cancer therapy. Starting from a known allosteric inhibitor, NMS-873, we systematically optimized this scaffold, in particular, by applying a benzene-to-acetylene isosteric replacement strategy, specific incorporation of F, and eutomer/distomer identification, which led to compounds that exhibited nanomolar biochemical and cell-based potency. In cellular pharmacodynamic assays, robust effects on biomarkers of p97 inhibition and apoptosis, including increased levels of ubiquitinated proteins, CHOP and cleaved caspase 3, were observed. Compound (
Language	English
Publishing date	2023-06-21
Publishing country	United States
Document type	Journal Article
ISSN	1948-5875
ISSN	1948-5875
DOI	10.1021/acsmedchemlett.3c00163
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Article: The breaking and mending of porphyrins: reductive coupling of secochlorin bisaldehydes

Akhigbe, Joshua / Samankumara, Lalith P / Brückner, Christian

Tetrahedron letters. 2012 July 4, v. 53, no. 27

2012

Abstract: The reaction of free base or Ni(II) complex secochlorin bisaldehydes 4H₂ and 4Ni regenerates the ultimate starting material of the bisaldehydes, meso-tetraphenylporphyrin 2H₂ and 2Ni, respectively. Depending on the reaction conditions employed (hydrazine ...

Abstract	The reaction of free base or Ni(II) complex secochlorin bisaldehydes 4H₂ and 4Ni regenerates the ultimate starting material of the bisaldehydes, meso-tetraphenylporphyrin 2H₂ and 2Ni, respectively. Depending on the reaction conditions employed (hydrazine hydrate in pyridine at reflux or hydrazine hydrate activated with sulfur in the presence of aqueous NaOH at ambient temperature), either porphyrin 2H₂ is formed together with known dihydroxymorpholinochlorin 9H₂ or known 2-hydroxychlorin 8H₂. Two different reaction pathways for the hydrazine reaction can be derived, either involving the formation of a meso-tetraphenyl-1,4,5-triazepinoporphyrin that loses spontaneously N₂ or a Wolff–Kishner-type pathway that also involves an intramolecular aldol-type reaction. Neither reaction is synthetically useful but both highlight in an impressive fashion the high thermodynamic stability of porphyrins. They also bring the ‘breaking and mending of porphyrin’ strategy to its ultimate conclusion by regenerating the starting porphyrin.
Keywords	ambient temperature ; chemical reactions ; chemical structure ; hydrazine ; nickel ; nitrogen ; porphyrins ; pyridines ; sodium hydroxide ; sulfur ; thermodynamics
Language	English
Dates of publication	2012-0704
Size	p. 3524-3526.
Publishing place	Elsevier Ltd
Document type	Article
ZDB-ID	204287-3
ISSN	1873-3581 ; 0040-4039
ISSN (online)	1873-3581
ISSN	0040-4039
DOI	10.1016/j.tetlet.2012.04.137
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Article ; Online: Bacteriochlorins with a Twist: Discovery of a Unique Mechanism to Red-Shift the Optical Spectra of Bacteriochlorins.

Guberman-Pfeffer, Matthew J / Greco, Jordan A / Samankumara, Lalith P / Zeller, Matthias / Birge, Robert R / Gascón, José A / Brückner, Christian

Journal of the American Chemical Society

2017 Volume 139, Issue 1, Page(s) 548–560

Abstract: Owing to their intense near infrared absorption and emission properties, to the ability to photogenerate singlet oxygen, or to act as photoacoustic imaging agents within the optical window of tissue, bacteriochlorins (2,3,12,13-tetrahydroporphyrins) ... ...

Abstract	Owing to their intense near infrared absorption and emission properties, to the ability to photogenerate singlet oxygen, or to act as photoacoustic imaging agents within the optical window of tissue, bacteriochlorins (2,3,12,13-tetrahydroporphyrins) promise to be of utility in many biomedical and technical applications. The ability to fine-tune the electronic properties of synthetic bacteriochlorins is important for these purposes. In this vein, we report the synthesis, structure determination, optical properties, and theoretical analysis of the electronic structure of a family of expanded bacteriochlorin analogues. The stepwise expansion of both pyrroline moieties in near-planar meso-tetraarylbacteriochlorins to morpholine moieties yields ruffled mono- and bismorpholinobacteriochlorins with broadened and up to 90 nm bathochromically shifted bacteriochlorin-like optical spectra. Intramolecular ring-closure reactions of the morpholine moiety with the flanking meso-aryl groups leads to a sharpened, blue-shifted wavelength λ
MeSH term(s)	Crystallography, X-Ray ; Models, Molecular ; Molecular Conformation ; Porphyrins/chemical synthesis ; Porphyrins/chemistry ; Quantum Theory ; Spectrophotometry, Ultraviolet
Chemical Substances	Porphyrins ; bacteriochlorin
Language	English
Publishing date	2017--11
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	3155-0
ISSN	1520-5126 ; 0002-7863
ISSN (online)	1520-5126
ISSN	0002-7863
DOI	10.1021/jacs.6b12419
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Article: Bacteriochlorins with a Twist: Discovery of a Unique Mechanism to Red-Shift the Optical Spectra of Bacteriochlorins

Guberman-Pfeffer, Matthew J / Birge Robert R / BruÌckner Christian / GascoÌn JoseÌ A / Greco Jordan A / Samankumara Lalith P / Zeller Matthias

Journal of the American Chemical Society. 2017 Jan. 11, v. 139, no. 1

2017

Abstract	Owing to their intense near infrared absorption and emission properties, to the ability to photogenerate singlet oxygen, or to act as photoacoustic imaging agents within the optical window of tissue, bacteriochlorins (2,3,12,13-tetrahydroporphyrins) promise to be of utility in many biomedical and technical applications. The ability to fine-tune the electronic properties of synthetic bacteriochlorins is important for these purposes. In this vein, we report the synthesis, structure determination, optical properties, and theoretical analysis of the electronic structure of a family of expanded bacteriochlorin analogues. The stepwise expansion of both pyrroline moieties in near-planar meso-tetraarylbacteriochlorins to morpholine moieties yields ruffled mono- and bismorpholinobacteriochlorins with broadened and up to 90 nm bathochromically shifted bacteriochlorin-like optical spectra. Intramolecular ring-closure reactions of the morpholine moiety with the flanking meso-aryl groups leads to a sharpened, blue-shifted wavelength Î»âââ band, bucking the general red-shifting trend expected for such linkages. A conformational origin of the optical modulations was previously proposed, but discrepancies between the solid state conformations and the corresponding solution state optical spectra defy simple structure-optical property correlations. Using density functional theory and excited state methods, we derive the molecular origins of the spectral modulations. About half of the modulation is due to ruffling of the bacteriochlorin chromophore. Surprisingly, the other half originates in the localized twisting of the Cáµ¦âCÎ±âCÎ±âCáµ¦ dihedral angle within the morpholine moieties. Our calculations suggest a predictable and large spectral shift (2.0 nm/deg twist) for morpholine deformations within these fairly flexible moieties. This morpholine moiety deformation can take place largely independently from the overall macrocycle conformation. The morpholinobacteriochlorins are thus excellent models for localized bacteriochlorin chromophore deformations that are suggested to also be responsible for the optical modulation of naturally occurring bacteriochlorophylls. We propose the use of morpholinobacteriochlorins as mechanochromic dyes in engineering and materials science applications.
Keywords	absorption ; deformation ; dyes ; engineering ; image analysis ; materials science ; models ; morpholine ; optical properties ; singlet oxygen ; wavelengths
Language	English
Dates of publication	2017-0111
Size	p. 548-560.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	3155-0
ISSN	1520-5126 ; 0002-7863
ISSN (online)	1520-5126
ISSN	0002-7863
DOI	10.1021%2Fjacs.6b12419
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Article ; Online: Syntheses, structures, modification, and optical properties of meso-tetraaryl-2,3-dimethoxychlorin, and two isomeric meso-tetraaryl-2,3,12,13-tetrahydroxybacteriochlorins.

Samankumara, Lalith P / Zeller, Matthias / Krause, Jeanette A / Brückner, Christian

Organic & biomolecular chemistry

2010 Volume 8, Issue 8, Page(s) 1951–1965

Abstract: The refined syntheses, modification, and first X-ray structural characterization of meso-tetraarylporphyrin-derived beta-tetraolbacteriochlorins are described. These investigations assign the relative stereochemistry of their two isomers (both cis-vic- ... ...

Abstract	The refined syntheses, modification, and first X-ray structural characterization of meso-tetraarylporphyrin-derived beta-tetraolbacteriochlorins are described. These investigations assign the relative stereochemistry of their two isomers (both cis-vic-diol pairs on the same or opposite sides of the porphyrin plane), an assignment that could not be provided by NMR, UV-vis or fluorescence spectroscopy, or mass spectrometry. Moreover, the first crystal structures of a 2-hydroxychlorin and a 2,3-dihydroxychlorin, as its dimethylether, are reported. Dihydroxylation and diimide reduction of the dimethoxychlorin result in the formation of stable mixed-functionality bacteriochlorins. The photophysical properties (UV-vis absorption and fluorescence emission) of all chromophores are contrasted against each other, delineating the electronic effects of diol substitution and conformational modulation. Lastly, the acid-induced dehydration/demethoxylation of the tetraol-, dioldimethoxy-, and tetramethoxybacteriochlorins to provide chlorins is delineated.
MeSH term(s)	Crystallography, X-Ray ; Isomerism ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Models, Molecular ; Porphyrins/chemical synthesis ; Porphyrins/chemistry ; Protons ; Spectrometry, Fluorescence ; Spectrophotometry, Ultraviolet
Chemical Substances	Porphyrins ; Protons ; bacteriochlorin ; meso-tetraaryl-2,3-dimethoxychlorin ; chlorin (2683-84-3)
Language	English
Publishing date	2010-04-21
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, Non-P.H.S.
ZDB-ID	2097583-1
ISSN	1477-0539 ; 1477-0520
ISSN (online)	1477-0539
ISSN	1477-0520
DOI	10.1039/b924539a
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